Imidazole → 5-(((tert-Butyldimethylsilyl)oxy)methyl)thiazol-2-amine

Participants

Reaction Steps

A solution of 5-(hydroxymethyl)-thiazol-2-ylamine (0.787 g, 6.05 mmol), TBDMSCl (1.003 g, 6.65 mmol) and imidazole (0.49 g, 7.26 mmol) in DMF (15 mL) is stirred at room temperature for 24 h. The reaction mixture is diluted with ether and water. The organic layer is washed with water (3×). The aqueous washings are backwashed with ether (2×). The organic layers are combined, dried over MgSO4 and condensed. The crude material is purified using a plug of silica and eluting with 1:1 petrol:ethyl acetate to give the product (0.656 g, 44%). 1H-NMR (400 MHz, d6-DMSO) =0.01 (s, 6H, 2×CH3), 0.82 (s, 9H, tBu), 4.61 (s, 2H, CH2), 4.74 (brs, 2H, NH2), 6.8 (s, 1H, CH). LCMS: Rt 2.62 min (92.7%). MS (MH+, m/z) 245.

Provenance & Evidence